3,4-Methylenedioxyamphetamine

Source: Wikipedia, the free encyclopedia.
See also:
ORTHO-MDA
Not to be confused with
2,3-methylenedioxyamphetamine; 4,4'-Methylenedianiline; or malondialdehyde
.

3,4-Methylenedioxyamphetamine
INN: Tenamfetamine
Clinical data
Routes of
administration		Oral, sublingual, insufflation, intravenous
ATC code
  • None
Legal status
Legal status
CYP extensively involved)
ExcretionRenal
Identifiers
  • 1-(2H-1,3-Benzodioxol-5-yl)propan-2-amine
JSmol)
  • NC(C)CC1=CC2=C(C=C1)OCO2
  • InChI=1S/C10H13NO2/c1-7(11)4-8-2-3-9-10(5-8)13-6-12-9/h2-3,5,7H,4,6,11H2,1H3 checkY
  • Key:NGBBVGZWCFBOGO-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

3,4-Methylenedioxyamphetamine (also known as MDA and sass) is an

recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance
and its possession and sale are illegal.

MDA is rarely sought as a recreational drug compared to other amphetamines; however, it remains widely used due to it being a primary metabolite,[2] the product of hepatic N-dealkylation,[3] of MDMA (ecstasy). It is also a common adulterant of illicitly produced MDMA.[4][5]

Uses

Medical

MDA currently has no accepted medical use.

Recreational

MDA is bought, sold, and used as a recreational 'love drug', due to its enhancement of mood and empathy.[6] A recreational dose of MDA is sometimes cited as being between 100 and 160 mg.[7]

Adverse effects

MDA can produce serotonergic neurotoxic effects in rodents,

neuroglia, though this subsides after use.[8]

Overdose

Symptoms of acute toxicity may include

hemorrhaging in the brain (stroke).[10][medical citation needed
]

Pharmacology

Pharmacodynamics

MDA is a

affinity for the α2A-, α2B-, and α2C-adrenergic receptors and serotonin 5-HT1A and 5-HT7 receptors.[16]

The (S)-

optical isomer as a psychostimulant, possessing greater affinity for the three monoamine transporters
.

In terms of the subjective and behavioral effects of MDA, it is thought that serotonin release is required for its empathogen-entactogen effects, release of dopamine and norepinephrine is responsible for its psychostimulant effects, dopamine release is necessary for its

addictive) effects, and direct agonism of the serotonin 5-HT2A receptor is causative of its psychedelic effects.[medical citation needed
]

Pharmacokinetics

The duration of the drug has been reported as about 6 to 8 hours.[7]

Chemistry

MDA is a

desmethyl
derivative of MDMA.

Synonyms

In addition to 3,4-methylenedioxyamphetamine, MDA is also known by other chemical synonyms such as the following:

  • α-Methyl-3,4-methylenedioxy-β-phenylethylamine
  • 1-(3,4-Methylenedioxyphenyl)-2-propanamine
  • 1-(1,3-Benzodioxol-5-yl)-2-propanamine

Synthesis

MDA is typically synthesized from essential oils such as safrole or piperonal. Common approaches from these precursors include:

Synthesis of MDA and related analogs from safrole

Detection in body fluids

MDA may be quantitated in blood, plasma or urine to monitor for use, confirm a diagnosis of poisoning or assist in the forensic investigation of a traffic or other criminal violation or a sudden death. Some drug abuse screening programs rely on hair, saliva, or sweat as specimens. Most commercial amphetamine immunoassay screening tests cross-react significantly with MDA and major metabolites of MDMA, but chromatographic techniques can easily distinguish and separately measure each of these substances. The concentrations of MDA in the blood or urine of a person who has taken only MDMA are, in general, less than 10% those of the parent drug.[27][28][29]

Derivatives

MDA constitutes part of the core structure of the β-adrenergic receptor agonist protokylol.

History

MDA was first synthesized by

ataractic by Smith, Kline & French in 1960, and as an anorectic under the trade name "Amphedoxamine" in 1961. MDA began to appear on the recreational drug scene around 1963 to 1964. It was then inexpensive and readily available as a research chemical from several scientific supply houses. Several researchers, including Claudio Naranjo and Richard Yensen, have explored MDA in the field of psychotherapy.[31][32]

Society and culture

MDA as prepared for recreational use

Name

When MDA was under development as a potential pharmaceutical drug, it was given the international nonproprietary name (INN) of tenamfetamine.

Legal status

Australia

MDA is schedule 9 prohibited substance under the Poisons Standards.[33] A schedule 9 substance is listed as a "Substances which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities."[33]

United States

MDA is a Schedule I controlled substance in the US.

Research

In 2010, the ability of MDA to invoke mystical experiences and alter vision in healthy volunteers was studied. The study concluded that MDA is a "potential tool to investigate mystical experiences and visual perception".[7]

A 2019 double-blind study administered both MDA and MDMA to healthy volunteers. The study found that MDA shared many properties with MDMA including entactogen and stimulant effects, but generally lasted longer and produced greater increases in psychedelic-like effects like complex imagery, synesthesia, and spiritual experiences.[34]

References

  1. ^ "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control]. Brazilian Health Regulatory Agency (in Brazilian Portuguese). Diário Oficial da União (published 25 July 2023). 24 July 2023. Archived from the original on 27 August 2023. Retrieved 27 August 2023.
  2. PMID 16876329
    .
  3. ^
    PMID 15228154
    .
  4. ^ "EcstasyData.org: Test Result Statistics: Substances by Year". EcstasyData.org. Retrieved 27 June 2017.
  5. ^ "Trans European Drug Information". idpc.net. Archived from the original on 4 November 2021. Retrieved 27 June 2017.
  6. PMID 8246240
    .
  7. ^
    PMID 21152030
    .
  8. ^
    PMID 24299738
    .
  9. PMID 11599334
    .
  10. ^ Diaz J (1996). How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall.
  11. PMID 22037049
    .
  12. PMID 17017961
    .
  13. ISBN 978-0-444-53235-0
    .
  14. PMID 19505264
    .
  15. S2CID 41352480
    .
  16. PMID 20126400
    .
  17. PMID 14477621
    .
  18. ^
    ISBN 978-0-9630096-3-0
    .
  19. PMID 2875058
    .
  20. ^
    doi:10.1002/cber.19100430126
    .
  21. PMID 5412110
    .
  22. doi:10.1039/C39740000307
    .
  23. doi:10.1248/jhs1956.38.571
    . Retrieved 20 June 2014.
  24. ISBN 978-0-9630096-0-9
    .
  25. ISSN 0368-1769
    .
  26. SSRN 3973132
    . Retrieved 11 February 2024.
  27. ^ Kolbrich EA, Goodwin RS, Gorelick DA, Hayes RJ, Stein EA, Huestis MA. Plasma pharmacokinetics of 3,4-methylenedioxymethamphetamine after controlled oral administration to young adults. Ther. Drug Monit. 30: 320–332, 2008.
  28. PMID 19168553
    .
  29. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 9th edition, Biomedical Publications, Seal Beach, California, 2011, pp. 1078–1080.
  30. ^ "The First MDA trip and the measurement of 'mystical experience' after MDA, LSD, and Psilocybin". Psychedelic research. 18 July 2008. Archived from the original on 13 July 2012.
  31. PMID 5631047
    .
  32. S2CID 41155810
    .
  33. ^ a b Poisons Standard (October 2015) comlaw.gov.au
  34. S2CID 106410946
    .

External links